N,N'-Dimethylethylenediamine → HCID 16064037, compound

HRID 421277Notes

Reaction equation

HRID 421277 reaction equation
[C:1]1(=[O:11])[NH:7][CH2:6][CH2:5][CH2:4][N:3]2[CH2:8][CH2:9][CH2:10][C@@H:2]12.[F:12][C:13]([F:47])([F:46])[C:14]1[CH:15]=[C:16]([C:24]([CH3:45])([CH3:44])[C:25]([N:27]([C:29]2[CH:30]=[N:31][C:32](Cl)=[CH:33][C:34]=2[C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=2[CH3:42])[CH3:28])=[O:26])[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1.CNCCNC.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.CCOC(C)=O.[Cu]I>[F:23][C:20]([F:21])([F:22])[C:18]1[CH:17]=[C:16]([C:24]([CH3:45])([CH3:44])[C:25]([N:27]([C:29]2[CH:30]=[N:31][C:32]([N:7]3[CH2:6][CH2:5][CH2:4][N:3]4[CH2:8][CH2:9][CH2:10][C@H:2]4[C:1]3=[O:11])=[CH:33][C:34]=2[C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=2[CH3:42])[CH3:28])=[O:26])[CH:15]=[C:14]([C:13]([F:47])([F:12])[F:46])[CH:19]=1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 10796Cesium carbonateHCID 235027842-(3,5-Bis(trifluoromethyl)phenyl)-N-(6-chloro-4-(4-fluoro-2-methylphenyl)pyrid-3-yl)-N,2-dimethylpropanamideHCID 51898145HCID 51898145, compound

Product 1

HCID 16064037HCID 16064037, compoundYield 21.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (9aS)-octahydro-1H-pyrrolo[1,2-a][1,4]diazepin-1-one (Polish Journal of Chemistry, 59(10-12), 1243-6; 1985) (31 mg, 0.201 mmol), 2-[3,5-bis(trifluoromethyl)phenyl]-N-[6-chloro-4-(4-fluoro-2-methylphenyl)-3-pyridinyl]-N,2-dimethylpropanamide [WO 2005/002577] (53 mg, 0.0996 mmol), N,N′-dimethyethylendiamine (224, 0.207 mmol), copper(I) iodide (38 mg, 0.200 mmol) and caesium carbonate (65 mg, 0.199 mmol) in 3 mL of dioxane was heated to 100° C. in a sealed vial overnight. Heating was continued for additional 2 days. It was diluted with 10 mL of EtOAc and extracted with water. The organics were dried (Na2SO4) and the solvent removed. The product was isolated by flash chromatography (silica, cyclohexane:EtOAc 90:10 to 30:70). Thus were obtained 14 mg of the target compound.

Workup

  1. temperatureHeating
  2. extractionextracted with water
  3. dry with materialThe organics were dried (Na2SO4)
  4. customthe solvent removed
  5. customThe product was isolated by flash chromatography (silica, cyclohexane:EtOAc 90:10 to 30:70)

Sources & evidence

ORD record
ord-28719863648a4e3b93c3c62fc59da81d
Source dataset
uspto-grants-2012_01
Patent number
US08097618B2

Reaction notes

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